Journal
POLYMER CHEMISTRY
Volume 5, Issue 24, Pages 7021-7033Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4py01102c
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Funding
- National Science Foundation [DMR-1308276]
- Institute for Critical Technologies and Applied Science at Virginia Tech
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Olefin cross-metathesis has been demonstrated to be a modular pathway for synthesis of a series of functionalized cellulose esters. As a proof of concept, cellulose acetate was acylated with two terminally olefinic acid chlorides, pent-4-enoyl chloride and undec-10-enoyl chloride, providing olefin-terminated cellulose esters with different side-chain lengths. These omega-unsaturated cellulose esters were then reacted with a variety of cross-metathesis partners, including acrylic acid, methyl acrylate, 2-hydroxyethyl acrylate, poly(ethylene glycol) methyl ether acrylate, and allyl alcohols, using Hoveyda-Grubbs' 2nd generation catalyst. Complete conversion to cross-metathesis products was achieved in reactions with acrylic acid or acrylates using 3-5 mol% catalyst at 40 degrees C within 1 h. We further demonstrate successful hydrogenation of these alpha,beta-unsaturated esters and acids, thereby eliminating the potential for radical-induced crosslinking during storage.
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